Palladium Catalyzed C-O Bond Formation: Synthesis of Aryl Benzoates
Keywords:
Palladium Catalyzed, Aryl Benzoates, carboxylic acids, aryl iodidesAbstract
A [Pd]-catalyzed intermolecular C-O bond formation strategy, is established towards the synthesis of aryl esters. Coupling of carboxylic acids with iodoarenes has been accomplished. Interestingly, water TBHP served as the reaction medium. This process found to be compatible with a good range of functional groups.
References
Reference:
1. (a) K. Fujiwara, T. Sato, Y. Sano, T. Norikura, R. Katoono, T. Suzuki, H. Matsue, J. Org. Chem. 2012, 77, 5161; (b) Y. Q. Ye, C. Negishi, Y. Hongo, H. Koshino, J. I. Onose, N. Abe, S. Takahashi, Bioorg. Med. Chem. 2014, 22, 2442.
2. (a) M. V. Khedkar, T. Sasaki and B. M. Bhanage, ACS Catal. 2013, 3, 287; (b) X. F. Cheng, Y. Li, Y. M. Su, F. Yin, J. Y. Wang, J. Sheng, H. U. Vora, X. S. Wang and J. Q. Yu, J. Am. Chem. Soc. 2013, 135, 1236; (c) J. N. Rosa, R. S. Reddy, N. R. Candeias, P. M. S. D. Cal and P. M. P. Gois, Org. Lett. 2010, 12, 2686; (d) Klare, J. E.; Tulevski, G. S.; Sugo, K.; de Picciotto, A.; White, K. A.; Nuckolls, C. J. Am. Chem. Soc. 2003, 125, 6030.
3. (a) R. Takise, K. Muto and J. Yamaguchi, Chem. Soc. Rev. 2017, 46, 5864; (b) K. W. Quasdorf, X. Tian and N. K. Garg, J. Am. Chem. Soc. 2008, 130, 14422–14423; (c) B. J. Li, Y. Z. Li, X. Y. Lu, J. Liu, B. T. Guan and Z. J. Shi, Angew. Chem. Int. Ed. 2008, 47, 10124; (d) T. Shimasaki, M. Tobisu and N. Chatani, Angew. Chem. Int. Ed. 2010, 49, 2929; (e) R. Takise, K. Itami and J. Yamaguchi, Org. Lett. 2016, 18, 4428.
4. (a) Lu, W.; Chen, J.; Liu, M.; Ding, J.; Gao, W.; Wu, H. Org. Lett. 2011, 13, 6114; (b) Chen, M.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. J. Org. Chem. 2015, 80, 1258.
5. D. Rankine, A. Avellaneda, M. R. Hill, C. J. Doonan, C. J. Sumby, Chem. Commun. 2012, 48, 10328.
6. Janina, G.; Adam, D.; Przemyslaw, M. Polym. J. Chem. 1990, 64, 317.
7. (a) R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 966; (b) J. Otera, Esterification: Methods, Reactions and Applications, Wiley, New York, 2003.; (c) J. Otera, Chem. Rev. 1993, 93, 1449–1470; (d) K. Ishihara, Tetrahedron 2009, 65, 1085; (e) A. K. Chakraborti and Shivani, J. Org. Chem. 2006, 71, 5785; (f) M. S. Carle, G. K. Shimokura and G. K. Murphy, Eur. J. Org. Chem. 2016, 3930.
8. (a) A. Shao, J. Zhan, N. Li, C. W. Chiang and A. Lei, J. Org. Chem. 2018, 83, 3582; (b) M. Zhang, R. Ruzi, N. Li, J. Xie and C. Zhu, Org. Chem. Front. 2018, 5, 749; (c) K. Padala and M. Jeganmohan, Chem. Commun. 2013, 49, 9651; (d) J. Wu, K. L. M. Hoang, M. L. Leow and X. W. Liu, Org. Chem. Front. 2015, 2, 502.
9. F. Luo, C. Pan, P. Qian and J. Cheng, Synthesis 2010, 2005.
10. (a) L. Zhang, G. Zhang, M. Zhang and J. Cheng, J. Org. Chem. 2010, 75, 7472; (b) J. J. Dai, J. H. Liu, D. F. Luo and L. Liu, Chem. Commun. 2011, 47, 677; (c) J. S. Ruso, N. Rajendiran and R. S. Kumaran, Tetrahedron Lett. 2014, 55, 2345.
11. (a) T. B. Petersen, R. Khan and B. Olofsson, Org. Lett. 2011, 13, 3462; (b) H. Xie, S. Yang, C. Zhang, M. Ding, M. Liu, J. Guo and F. Zhang, J. Org. Chem. 2017, 82, 5250; (c) T. Dohi, D. Koseki, K. Sumida, K. Okada, S. Mizuno and A. Kato, Adv. Synth. Catal. 2017, 359, 3503; (d) B. Bhattarai, J. H. Tay and P. Nagorn, Chem. Commun. 2015, 51, 5398.
12. (a) F. Ullmann, Ber. Dtsch. Chem. Ges. 1904, 37, 853; (b) J. Lindley, Tetrahedron 1984, 40, 1433; (c) Y. C. Tan, J. T. Muñoz-Molina, G. C. Fu and J. C. Peters, Chem. Sci. 2014, 5, 2831; (d) B. J. Shields, B. Kudisch, G. D. Scholes and A. G. Doyle, J. Am. Chem. Soc. 2018, 140, 3035; (e) W. Zhou, J. W. Schultz, N. P. Rath and L. M. Mirica, J. Am. Chem. Soc. 2015, 137, 7604; (f) Y. W. Zheng, P. Ye, B. Chen, Q. Y. Meng, K. Feng, W. Wang, L. Z. Wu and C. H. Tung, Org. Lett. 2017, 19, 2206.
13. (a) D.L. Zhu, H. X. Li, Z. M. Xu, H. Y. Li, D. J. Young and J. P. Lang, Org. Chem. Front. 2019, 6, 2353; (b) Tue B. Petersen, Rehan Khan, and Berit Olofsson, Org. Lett. 2011, 13, 3462.
14. a) L. Mahendar, J. Krishna, A. G. K. Reddy, B. V. Ramulu and G. Satyanarayana, Org. Lett. 2012, 14, 628; b) D. R. Kumar and G. Satyanarayana, Org. Lett. 2015, 17, 5894; c) J. Krishna, A. G. K. Reddy and G. Satyanarayana, Adv. Synth. Catal. 2015, 357, 3597; (d) B. Suchand and G. Satyanarayana, J. Org. Chem. 2017, 82, 372; (e) B. Suchand and G. Satyanarayana, Eur. J. Org. Chem. 2018, 2233; f) K. Ramesh, and G. Satyanarayana, Green Chem. 2018, 20, 369; g) K. Ramesh, S. Basuli, and G. Satyanarayana, Eur. J. Org. Chem. 2018, 2171.
15. B. Suchand, and G. Satyanarayana, J. Org. Chem. 2016, 81, 6409.
1. (a) K. Fujiwara, T. Sato, Y. Sano, T. Norikura, R. Katoono, T. Suzuki, H. Matsue, J. Org. Chem. 2012, 77, 5161; (b) Y. Q. Ye, C. Negishi, Y. Hongo, H. Koshino, J. I. Onose, N. Abe, S. Takahashi, Bioorg. Med. Chem. 2014, 22, 2442.
2. (a) M. V. Khedkar, T. Sasaki and B. M. Bhanage, ACS Catal. 2013, 3, 287; (b) X. F. Cheng, Y. Li, Y. M. Su, F. Yin, J. Y. Wang, J. Sheng, H. U. Vora, X. S. Wang and J. Q. Yu, J. Am. Chem. Soc. 2013, 135, 1236; (c) J. N. Rosa, R. S. Reddy, N. R. Candeias, P. M. S. D. Cal and P. M. P. Gois, Org. Lett. 2010, 12, 2686; (d) Klare, J. E.; Tulevski, G. S.; Sugo, K.; de Picciotto, A.; White, K. A.; Nuckolls, C. J. Am. Chem. Soc. 2003, 125, 6030.
3. (a) R. Takise, K. Muto and J. Yamaguchi, Chem. Soc. Rev. 2017, 46, 5864; (b) K. W. Quasdorf, X. Tian and N. K. Garg, J. Am. Chem. Soc. 2008, 130, 14422–14423; (c) B. J. Li, Y. Z. Li, X. Y. Lu, J. Liu, B. T. Guan and Z. J. Shi, Angew. Chem. Int. Ed. 2008, 47, 10124; (d) T. Shimasaki, M. Tobisu and N. Chatani, Angew. Chem. Int. Ed. 2010, 49, 2929; (e) R. Takise, K. Itami and J. Yamaguchi, Org. Lett. 2016, 18, 4428.
4. (a) Lu, W.; Chen, J.; Liu, M.; Ding, J.; Gao, W.; Wu, H. Org. Lett. 2011, 13, 6114; (b) Chen, M.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. J. Org. Chem. 2015, 80, 1258.
5. D. Rankine, A. Avellaneda, M. R. Hill, C. J. Doonan, C. J. Sumby, Chem. Commun. 2012, 48, 10328.
6. Janina, G.; Adam, D.; Przemyslaw, M. Polym. J. Chem. 1990, 64, 317.
7. (a) R. C. Larock, Comprehensive Organic Transformations, VCH, New York, 1989, p. 966; (b) J. Otera, Esterification: Methods, Reactions and Applications, Wiley, New York, 2003.; (c) J. Otera, Chem. Rev. 1993, 93, 1449–1470; (d) K. Ishihara, Tetrahedron 2009, 65, 1085; (e) A. K. Chakraborti and Shivani, J. Org. Chem. 2006, 71, 5785; (f) M. S. Carle, G. K. Shimokura and G. K. Murphy, Eur. J. Org. Chem. 2016, 3930.
8. (a) A. Shao, J. Zhan, N. Li, C. W. Chiang and A. Lei, J. Org. Chem. 2018, 83, 3582; (b) M. Zhang, R. Ruzi, N. Li, J. Xie and C. Zhu, Org. Chem. Front. 2018, 5, 749; (c) K. Padala and M. Jeganmohan, Chem. Commun. 2013, 49, 9651; (d) J. Wu, K. L. M. Hoang, M. L. Leow and X. W. Liu, Org. Chem. Front. 2015, 2, 502.
9. F. Luo, C. Pan, P. Qian and J. Cheng, Synthesis 2010, 2005.
10. (a) L. Zhang, G. Zhang, M. Zhang and J. Cheng, J. Org. Chem. 2010, 75, 7472; (b) J. J. Dai, J. H. Liu, D. F. Luo and L. Liu, Chem. Commun. 2011, 47, 677; (c) J. S. Ruso, N. Rajendiran and R. S. Kumaran, Tetrahedron Lett. 2014, 55, 2345.
11. (a) T. B. Petersen, R. Khan and B. Olofsson, Org. Lett. 2011, 13, 3462; (b) H. Xie, S. Yang, C. Zhang, M. Ding, M. Liu, J. Guo and F. Zhang, J. Org. Chem. 2017, 82, 5250; (c) T. Dohi, D. Koseki, K. Sumida, K. Okada, S. Mizuno and A. Kato, Adv. Synth. Catal. 2017, 359, 3503; (d) B. Bhattarai, J. H. Tay and P. Nagorn, Chem. Commun. 2015, 51, 5398.
12. (a) F. Ullmann, Ber. Dtsch. Chem. Ges. 1904, 37, 853; (b) J. Lindley, Tetrahedron 1984, 40, 1433; (c) Y. C. Tan, J. T. Muñoz-Molina, G. C. Fu and J. C. Peters, Chem. Sci. 2014, 5, 2831; (d) B. J. Shields, B. Kudisch, G. D. Scholes and A. G. Doyle, J. Am. Chem. Soc. 2018, 140, 3035; (e) W. Zhou, J. W. Schultz, N. P. Rath and L. M. Mirica, J. Am. Chem. Soc. 2015, 137, 7604; (f) Y. W. Zheng, P. Ye, B. Chen, Q. Y. Meng, K. Feng, W. Wang, L. Z. Wu and C. H. Tung, Org. Lett. 2017, 19, 2206.
13. (a) D.L. Zhu, H. X. Li, Z. M. Xu, H. Y. Li, D. J. Young and J. P. Lang, Org. Chem. Front. 2019, 6, 2353; (b) Tue B. Petersen, Rehan Khan, and Berit Olofsson, Org. Lett. 2011, 13, 3462.
14. a) L. Mahendar, J. Krishna, A. G. K. Reddy, B. V. Ramulu and G. Satyanarayana, Org. Lett. 2012, 14, 628; b) D. R. Kumar and G. Satyanarayana, Org. Lett. 2015, 17, 5894; c) J. Krishna, A. G. K. Reddy and G. Satyanarayana, Adv. Synth. Catal. 2015, 357, 3597; (d) B. Suchand and G. Satyanarayana, J. Org. Chem. 2017, 82, 372; (e) B. Suchand and G. Satyanarayana, Eur. J. Org. Chem. 2018, 2233; f) K. Ramesh, and G. Satyanarayana, Green Chem. 2018, 20, 369; g) K. Ramesh, S. Basuli, and G. Satyanarayana, Eur. J. Org. Chem. 2018, 2171.
15. B. Suchand, and G. Satyanarayana, J. Org. Chem. 2016, 81, 6409.
Additional Files
Published
2021-08-28
Issue
Section
Research Articles
License
Copyright (c) 2020 Mapana Journal of Sciences
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
